NP-MRD: Showing NP-Card for 4-[(r)-[(2s,5r)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](hydroxy)methyl]quinolin-6-ol (NP0213699)

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Record Information

Version

2.0

Created at

2022-09-05 12:45:38 UTC

Updated at

2022-09-05 12:45:38 UTC

NP-MRD ID

NP0213699

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[(r)-[(2s,5r)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](hydroxy)methyl]quinolin-6-ol

Description

Cupreine belongs to the class of organic compounds known as cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]Octane moiety. Cupreine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 4-[(r)-[(2s,5r)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](hydroxy)methyl]quinolin-6-ol is found in Cinchona calisaya and Tinadendron noumeanum. 4-[(r)-[(2s,5r)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](hydroxy)methyl]quinolin-6-ol was first documented in 2008 (PMID: 19829750). Based on a literature review a small amount of articles have been published on Cupreine (PMID: 35293212) (PMID: 27340439) (PMID: 26223465) (PMID: 20545337).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 48  0  0  0  0  0  0  0  0999 V2000
    4.0707    1.9939   -0.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2725    0.7114   -0.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5117   -0.4121    0.2700 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4707   -0.0938    1.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1698   -0.6274    0.8865 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2203   -2.0778    0.7760 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4606   -2.5568    0.0514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9198   -1.3400   -0.7741 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6657   -0.8030   -1.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8323   -0.0468   -0.3848 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6221   -0.0986   -0.6894 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7808    0.4776   -1.9742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3837    0.7822    0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833    1.7861    0.9455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5431    2.6265    1.7657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8705    2.4433    1.8491 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4753    1.4622    1.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8579    1.2751    1.2626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5084    0.2838    0.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7859   -0.5612   -0.2350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4263   -1.5722   -0.9305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4097   -0.3999   -0.3642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7805    0.5994    0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6938    2.7717   -0.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2489    2.3617    0.4819 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1515    0.4663   -0.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2737   -1.0730    0.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6718   -0.6127    2.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3182    0.9579    1.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3678   -2.3998    0.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1156   -2.5194    1.7801 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2688   -3.4350   -0.5820 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2487   -2.7894    0.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6543   -1.6843   -1.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195   -0.2153   -2.2953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0952   -1.7149   -1.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1868    0.9835   -0.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9389   -1.1404   -0.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5266    1.4280   -1.8690 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2614    1.9951    0.9345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0596    3.4305    2.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4289    1.9302    1.8989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5863    0.1622    0.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4056   -1.6890   -0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8963   -1.0657   -0.9998 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
 11 13  1  0
 13 23  1  0
 23 22  2  0
 22 20  1  0
 20 21  1  0
 20 19  2  0
 19 18  1  0
 18 17  2  0
 17 16  1  0
 16 15  2  0
 15 14  1  0
  5 10  1  0
 14 13  2  0
  3  8  1  0
 17 23  1  0
 12 39  1  0
 11 38  1  6
 10 37  1  1
  9 35  1  0
  9 36  1  0
  8 34  1  6
  7 32  1  0
  7 33  1  0
  6 30  1  0
  6 31  1  0
  4 28  1  0
  4 29  1  0
  3 27  1  1
  2 26  1  0
  1 24  1  0
  1 25  1  0
 22 45  1  0
 21 44  1  0
 19 43  1  0
 18 42  1  0
 15 41  1  0
 14 40  1  0
M  END


  Mrv1652309052214452D          

 23 26  0  0  1  0            999 V2000
    3.1464   -2.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1464   -1.8166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8608   -1.4041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8608   -0.5791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5753   -0.1666    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7128   -0.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7128   -1.2666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5753   -1.8166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2898   -1.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2898   -0.5791    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0043   -0.1666    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7187   -0.5791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0043    0.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2898    1.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2898    1.8959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0043    2.3084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7187    1.8959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4332    2.3084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1477    1.8959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1477    1.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8621    0.6584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4332    0.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7187    1.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 13 23  2  0  0  0  0
 17 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0213699

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]([C@@H]1CC2CCN1C[C@@H]2C=C)C1=C2C=C(O)C=CC2=NC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H22N2O2/c1-2-12-11-21-8-6-13(12)9-18(21)19(23)15-5-7-20-17-4-3-14(22)10-16(15)17/h2-5,7,10,12-13,18-19,22-23H,1,6,8-9,11H2/t12-,13?,18-,19+/m0/s1

> <INCHI_KEY>
VJFMSYZSFUWQPZ-BPBOJLQBSA-N

> <FORMULA>
C19H22N2O2

> <MOLECULAR_WEIGHT>
310.397

> <EXACT_MASS>
310.168127956

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
33.938663036737985

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(R)-[(2S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](hydroxy)methyl]quinolin-6-ol

> <JCHEM_LOGP>
1.9580330250756812

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.950910919880602

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.756924464821479

> <JCHEM_PKA_STRONGEST_BASIC>
8.954043083117359

> <JCHEM_POLAR_SURFACE_AREA>
56.59

> <JCHEM_REFRACTIVITY>
90.21130000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-[(R)-[(2S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](hydroxy)methyl]quinolin-6-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       5.873  -4.931   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.873  -3.391   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.207  -2.621   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.207  -1.081   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       8.541  -0.311   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       8.797  -1.338   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.797  -2.364   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.541  -3.391   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.874  -2.621   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.874  -1.081   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.208  -0.311   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.542  -1.081   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      11.208   1.229   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.874   1.999   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.874   3.539   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      11.208   4.309   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      12.542   3.539   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.875   4.309   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.209   3.539   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.209   1.999   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      16.543   1.229   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      13.875   1.229   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.542   1.999   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   23                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   13   17                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Value	Source
6'-Hydroxycinchonidine	MeSH
6'-Hydroxycinchonidine dihydrochloride	MeSH
6'-Hydroxycinchonidine monohydrochloride	MeSH
6'-Hydroxycinchonidine, (9S)-isomer	MeSH
O-Demethylquinidien	MeSH
O-Desmethylquinidine	MeSH
Cupreidine	MeSH

Chemical Formula

C₁₉H₂₂N₂O₂

Average Mass

310.3970 Da

Monoisotopic Mass

310.16813 Da

IUPAC Name

4-[(R)-[(2S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](hydroxy)methyl]quinolin-6-ol

Traditional Name

4-[(R)-[(2S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](hydroxy)methyl]quinolin-6-ol

CAS Registry Number

Not Available

SMILES

O[C@@H]([C@@H]1CC2CCN1C[C@@H]2C=C)C1=C2C=C(O)C=CC2=NC=C1

InChI Identifier

InChI=1S/C19H22N2O2/c1-2-12-11-21-8-6-13(12)9-18(21)19(23)15-5-7-20-17-4-3-14(22)10-16(15)17/h2-5,7,10,12-13,18-19,22-23H,1,6,8-9,11H2/t12-,13?,18-,19+/m0/s1

InChI Key

VJFMSYZSFUWQPZ-BPBOJLQBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cinchona calisaya	LOTUS Database	35616633
Guettarda noumeana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]Octane moiety.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Cinchona alkaloids

Sub Class

Not Available

Direct Parent

Cinchona alkaloids

Alternative Parents

Substituents

Cinchonan-skeleton
4-quinolinemethanol
Hydroxyquinoline
Quinoline
Quinuclidine
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Piperidine
Pyridine
Benzenoid
Heteroaromatic compound
1,2-aminoalcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Amine
Alcohol
Aromatic alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.96	ChemAxon
pKa (Strongest Acidic)	9.76	ChemAxon
pKa (Strongest Basic)	8.95	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	56.59 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	90.21 m³·mol⁻¹	ChemAxon
Polarizability	33.94 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00026411

Chemspider ID

389881

KEGG Compound ID

C06530

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441075

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lavios A, Sanz-Marco A, Vila C, Munoz MC, Pedro JR, Blay G: Metal-Free Diastereo- and Enantioselective Dearomative Formal [3 + 2] Cycloaddition of 2-Nitrobenzofurans and Isocyanoacetate Esters. Org Lett. 2022 Mar 25;24(11):2149-2154. doi: 10.1021/acs.orglett.2c00427. Epub 2022 Mar 16. [PubMed:35293212 ]
Bryant LA, Fanelli R, Cobb AJ: Cupreines and cupreidines: an established class of bifunctional cinchona organocatalysts. Beilstein J Org Chem. 2016 Mar 7;12:429-43. doi: 10.3762/bjoc.12.46. eCollection 2016. [PubMed:27340439 ]
Aitken LS, Hammond LE, Sundaram R, Shankland K, Brown GD, Cobb AJ: Asymmetric cyclopropanation of conjugated cyanosulfones using a novel cupreine organocatalyst: rapid access to delta(3)-amino acids. Chem Commun (Camb). 2015 Sep 11;51(70):13558-61. doi: 10.1039/c5cc05158d. [PubMed:26223465 ]
Chen WB, Wu ZJ, Pei QL, Cun LF, Zhang XM, Yuan WC: Highly enantioselective construction of spiro[4H-pyran-3,3'-oxindoles] through a domino Knoevenagel/Michael/cyclization sequence catalyzed by cupreine. Org Lett. 2010 Jul 16;12(14):3132-5. doi: 10.1021/ol1009224. [PubMed:20545337 ]
Dodda R, Goldman JJ, Mandal T, Zhao CG, Broker GA, Tiekink ER: Synthesis of 2,3,4-Trisubstituted Thiochromanes using an Organocatalytic Enantioselective Tandem Michael-Henry Reaction. Adv Synth Catal. 2008 Feb 26;350(4):537-541. doi: 10.1002/adsc.200700331. [PubMed:19829750 ]
LOTUS database [Link]

Showing NP-Card for 4-[(r)-[(2s,5r)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](hydroxy)methyl]quinolin-6-ol (NP0213699)

MOL for NP0213699 (4-[(r)-[(2s,5r)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](hydroxy)methyl]quinolin-6-ol)

3D MOL for NP0213699 (4-[(r)-[(2s,5r)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](hydroxy)methyl]quinolin-6-ol)

3D SDF for NP0213699 (4-[(r)-[(2s,5r)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](hydroxy)methyl]quinolin-6-ol)

3D-SDF for NP0213699 (4-[(r)-[(2s,5r)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](hydroxy)methyl]quinolin-6-ol)

PDB for NP0213699 (4-[(r)-[(2s,5r)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](hydroxy)methyl]quinolin-6-ol)

3D PDB for NP0213699 (4-[(r)-[(2s,5r)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](hydroxy)methyl]quinolin-6-ol)

SMILES for NP0213699 (4-[(r)-[(2s,5r)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](hydroxy)methyl]quinolin-6-ol)

INCHI for NP0213699 (4-[(r)-[(2s,5r)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](hydroxy)methyl]quinolin-6-ol)

Structure for NP0213699 (4-[(r)-[(2s,5r)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](hydroxy)methyl]quinolin-6-ol)

3D Structure for NP0213699 (4-[(r)-[(2s,5r)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](hydroxy)methyl]quinolin-6-ol)